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Enterprises are increasingly outsourcing network management (e.g., troubleshooting routing issues) to reduce cost and improve efficiency, either by hiring third-party contractors or by outsourcing to third-party vendors. Unfortunately, recent events have shown that this outsourcing model has become a new source of network incidents in customer networks. In this work, we argue that a risk-aware outsourcing approach is needed that enables customers to measure and assess risk transparently and make informed decisions to minimize harm. We first concretely define the notion of risk in the context of outsourced network management and then present an end-to-end framework, called Heimdall, which enables enterprises to assess, monitor, and respond to risk. Heimdall automatically builds a dependency graph to accurately assess the risk of an outsourced task, and uses a fine-grained reference monitor to monitor and mitigate potential risks during operation. Our expert validation results show that Heimdall effectively controls risk for outsourced network operations, resolving 92% of practical issues at the minimal risk level while incurring only a marginal timing overhead of approximately 7%.